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Ex-President Donald Trump has consistently expressed his desire to see critics investigated, exerting influence on the Justice Department to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay further, it's killing our reputation and trustworthiness," the president wrote last month in a social media message.

"They impeached me, and indicted me (5 times!)" he said, mentioning the multiple legal proceedings he encountered after leaving the White House in 2021 and James's lawsuit.

Each have subsequently been charged, in situations that many specialists have stated appear to be driven by politics and challenging to succeed in court.

But the latest allegations against a Trump critic, former security advisor John Bolton, differ significantly, legal experts and ex-prosecutors assert.

"In my opinion, contrasting Bolton's case to James' is like equating apples to oranges," said Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

The Details of the Legal Situation

Bolton has been formally charged on federal charges pertaining to the supposed mishandling of classified information. After leaving the White House in 2019, he has become a vocal presidential opponent, even to describe him "stunningly uninformed" and unfit for office in his memoir.

Specialists say that while there may be political reasons to target Bolton, the procedures used to obtain an indictment and the proof compiled against him indicate a potentially more substantial legal argument than the Justice Department presented against James.

"This misconduct that's being claimed is simultaneously more severe and appears to have taken place over a significant duration," commented Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his tenure as Trump's security advisor, and after his 2019 White House departure, authorities claimed that Bolton put the country at risk by improperly keeping and sending sensitive documents to relatives using insecure means, including AOL. Several of the documents were marked top secret.

The indictment states that at one point a hacker accessed to Bolton's account where files were kept and sent an apparent threat to cause "the biggest scandal since Hillary [Clinton]'s emails were leaked".

Bolton entered a not guilty plea during a hearing on recently to 18 separate charges of mishandling sensitive materials.

Retribution or a Substantial Legal Argument?

The timing of his charge - arriving on the heels of charges against Comey - has renewed questions about political pressure on the legal system.

Trump once suggested Bolton should be in jail, and called him a "sleazebag". Bolton, for his role, wrote a publication about his experience in the Trump administration that was highly critical of the president.

"There's no question that the schedule of this indictment, when paired with additional cases, has prompted questions about the validity of these allegations, and why these counts are being brought now," stated Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he added, "should the DOJ is able to demonstrate the allegations stated and show the material is correctly classified, his conduct may very well have broken the statute".

Charging such a senior figure for improperly handling classified documents is "uncommon" but not unprecedented, noted Carrie Cordero, a senior fellow at the Center for a New American Security.

"Situations that concern sensitive materials pose challenges to try, but they can and are filed against both low-level and senior officials, from time to time," she said.

Similarities to Investigations into Trump and President

Trump similarly faced charges of wrongfully storing classified documents at his Mar-a-Lago resort in Florida and hindering their recovery, but that matter was ultimately thrown out by a federal judge and negated by his return as leader.

A independent investigator additionally determined that ex-President Joe Biden wrongfully maintained sensitive materials from his period as second-in-command, but did not criminally charge him.

Bolton's situation shares characteristics to Trump's sensitive materials issues, noted Mr Lesko, who also held a top security role at the Justice Department.

Strict protocols regulate the handling of classified documents. To secure a guilty verdict, the government must demonstrate that Bolton knew the information he was transmitting was classified, and he had to knowingly transmit it to someone without authorization to obtain it.

"Because of the classified character of the information at issue in this case, we don't have a great deal of particulars about the reasons the government believes elements like the personal notes and the other material he shared by electronic message, and the reason there were classified," explained Mr Jaffer.

A More Conventional Legal Action

The procedure by which the Justice Department brought this case will be closely examined, after Trump publicly posted his wish to see his critics charged and some of those charges materialized.

But Mr Lesko said in Bolton's situation, prosecutors appear to have followed protocol.

"This Bolton prosecution and eventually the indictment appeared to have observed the standard procedure including the regulations and standards within the DOJ," he said.

Unlike Comey's brief, two-page charge, Bolton's was a increasingly "traditional" filing that "explicitly sets forth the particulars concerning the circumstances and circumstances here," Mr Lesko said.

"It seems reasonably aligned with a long line of cases... where public servants improperly handled and transmitted classified material."